I have no problem telling an operator if their machines aren't working. In fact, at our league location, I will often send the operator an email with the issues I've noticed so he can fix them before league night.
As for machines in poor condition, I never hesitate to tell an operator that their machines aren't up to snuff. Maybe they make some money in poor condition, but I'd wager that is money that is spent by a series of people who walk up, pop in 50 cents and then walk away disgusted. It does the hobby a disservice to have machines that aren't well maintained on location, because it discourages new players from trying again.
I also light them up on pinball map and Yelp.
Does that make me a dick? Maybe. I'd like to think more along the lines of crusader.